After the signing of Tupac Shakur to Death Row in September 1995, a rivalry was sparked between Death Row and the east coast's Bad Boy Entertainment. Death Row became a divided label, with Suge Knight demanding every rapper on the label diss an assortment of east coast artists hailing from or affiliated with Bad Boy. Having already thrown in on the Ruthless Records/Death Row conflict, Kurupt and Daz joined in the feud with their single "New York, New York," featuring Snoop Dogg; the song was interpreted as a diss against NYC and although it did not diss anyone specifically, it incited the response "L.A., L.A." by NY rappers Capone-N-Noreaga, Mobb Deep & Tragedy Khadafi. The duo's album, Dogg Food, became highly successful, despite being the first Death Row release not produced by Dr. Dre. Dr. Dre did, however, mix the album.

The time after Dogg Food's release was a hectic one for Death Row. Artists discouraged by the rising conflict included RBX, who left the label; Lady of Rage, whose project was continually postponed; and Dr. Dre himself, who began to resent Suge's controversial strong-arm tactics and thirst for the spotlight. When Dre jumped ship for Aftermath Entertainment, Daz became the main producer for Death Row, handling much of Tupac Shakur's All Eyez on Me and Snoop Dogg's Tha Doggfather, on which Kurupt was featured relatively sparingly, in contrast to his former high profile on label projects. Even though Kurupt was a member of the DPG, he developed a very strong friendship with Tupac and the Outlawz during the mid 1990s.

Tupac Shakur's 1996 murder began a mass exodus of artists from Death Row Records. Kurupt was one of the first to leave, preceded only by Nate Dogg; he initially signed with A&M, on which he founded an imprint, Antra Records. It was through this deal Brown released his debut solo album Kuruption! in 1998, with appearances by Dr. Dre, Buckshot, and former foe N.O.R.E. The video for the single, "Ask Yourself a Question" was directed by writer-journalist-filmmaker Barry Michael Cooper (who wrote the screenplays for "New Jack City", "Sugar Hill", and "Above The Rim"); it featured Dr. Dre, producer of the song. The video was filmed in Philadelphia, Pa., in November, 1998.

Though the double-disc effort featured only a bit of Daz production, he and his former groupmate were still on good terms; when Dillinger followed in his tracks and left Death Row in 1999, he produced several tracks for his groupmate's second album Tha Streetz Iz a Mutha, marking the end of Kurupt's tenure at Antra. The record featured a widespread diss track called "Calling Out Names," on which Kurupt called out various rappers, including DMX, accusing the east coaster of having an affair with his then fiance Foxy Brown. During this time, he linked up with fellow Californian Ras Kass, Wu-Tang Clan-affiliate Killah Priest and former Universal Records wonder Canibus to form a group called The HRSMN; despite repeated promises of an album, the group's only release has been an unfinished white label.

While Suge owned rights to Tha Dogg Pound name, Kurupt and Daz formed the core of an extended family called DPG (Dogg Pound Gangstaz)/DPGC (Dogg Pound Gangsta Crips), the latter of which also prominently featured Nate Dogg, Snoop Dogg, Soopafly, and others intermittently. Daz and Kurupt went on to release Dillinger & Young Gotti under the name DPG, which garnered lukewarm reviews.[3] Kurupt's following solo album for Artemis Records, Space Boogie: Smoke Oddessey, fared better, with production from Daz and up-and-coming producer Fredwreck; his then-fiancee, the late Natina Reed, provided the hook for the single "It's Over."

After an unofficial remix/compilation Dogg Pound album called 2002 in early 2002, questions began to arise as to the status of Tha Dogg Pound vs. Death Row. While the duo officially said they weren't sure, Kurupt signed back to Death Row in exchange for the role of Vice President[citation needed]. This apparently shocked his groupmates, especially Daz, who'd had a much more volatile falling-out with Knight; a verbal war erupted wherein Kurupt and Daz repeatedly dissed each other viciously, on records and in interviews.[4][5] While this was going on, Kurupt was mentoring a new roster of Death Row artists, including Spider Loc, Crooked I, and Eastwood; he also began work on his next album, Against tha Grain, and formed a new group: The Riflemen,[6] consisting of Kurupt, Mobb Deep, Jayo Felony, 40 Glocc, and The Alchemist, though the possibility of a record from this ensemble has seemingly faded over time.

More hurt by the conflict than he let on,[7] Kurupt continued to work disses into his solo album; a bootleg version of the project, Originals, was released in 2004 after repeated delays of its official release, as well as those of Crooked I and other Death Row artists. In 2005, Snoop Dogg began acting as a diplomat between the two parties, and Tha Dogg Pound reunited under its original moniker in April of that year at a west coast unity event hosted by Snoop.[8]Against tha Grain was released, but by that time Kurupt had already left the label a second time, and publicly denounced the disses inherent in the record; an EP called Against tha Grain E.P. has also surfaced, containing said disses to his cohorts. Since their reunion, Kurupt has claimed both members got over their previous problems with no issue.[9]

Kurupt and Daz released Dillinger & Young Gotti II: The Saga Continuez in 2005, Cali iz Active (as DPG with Snoop Dogg)[10] in 2006, and Dogg Chit in 2007; while he originally touted Dogg Chit as the heir to Dogg Food's legacy,[1] he has since stated that none of the group's intermittent releases are to be considered actual albums—more like mixtapes, and that the upcoming 100 Wayz (originally titled Westcoast Aftershocc) is to be considered the second actual Dogg Pound release.[9] '06 also saw the release of Snoop Dogg's album Tha Blue Carpet Treatment, on which Kurupt appeared. After putting out Digital Smoke with J. Wells, Brown also released an album with his younger brother Roscoe entitled The Frank and Jess Story. Kurupt appeared on Snoop Dogg's 2008 album Ego Trippin'.

Before 100 Wayz, Tha Dogg Pound's Gangsta Grillz mixtape was released, hosted by DJ Drama;,[11] followed by an album called BlaQKout with DJ Quik due out on April 28, 2009[12]—the single for which, "Fuck Y'all," is a diss to former Quik partners AMG, Hi-C and 2nd II None.

Kurupt has been featured on many tracks with other independent artists over the last few years and released his first solo album in four years, Streetlights, on April 20, 2010. Kurupt is currently recording with MC Eiht, King T, Jayo Felony, B.G. Knocc Out, Tha Chill, and Sir Jinx for a hip hop group project called "1st Generation".[13]

Kurupt’s plans for 2012 include the release of the long anticipated HRSMN album, 'The Academy' album which is a compilation album of collaborations between various artists and a guest feature on the single ‘Hey Girl’ alongside Joell Ortiz (Slaughterhouse) and Big Dave (rapper) taken from Big Dave’s debut album ‘Self Made’. Following the death of his son's Tren's mother Natina Reed (of R&B girl group Blaque) in a tragic car accident in Atlanta,[14] planned to release the DJ Nik Bean-hosted mixtape, Money, Bitches, Power on Nov. 7, 2012 but it was delayed.[15] The mixtape will feature E-40, Crooked I, Masta Killa, RBX, Ty Dolla Sign, The Rejectz and more.[16] It now is scheduled to be released on May 1, 2013.

Despite Kurupt's middling success with the record-buying public and post-1990s fade into obscurity, he has had an outsized influence among fellow rappers and is considered among the great "rappers' rappers" in hip-hop history. Kendrick Lamar cited Kurupt in a 2014 interview as one of his three most significant influences, alongside 2Pac and Ice Cube (the latter for lyrical content only).[17] In 'Til' I Collapse from 2002's The Eminem Show, Eminem ranked Kurupt seventh on his personal list of greatest MCs, behind, in order, Redman, Jay Z, 2Pac, Notorious B.I.G., Andre 3000, Jadakiss, Kurupt and Nas.